Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

3. Acids and Bases

Reaction Mechanism

Organic Chemistry

3. Acids and Bases

Reaction Mechanism

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1:12 minutes

Problem 56d

Textbook Question

Show an arrow-pushing mechanism that forms the product on the right from the reactant at left. Only one arrow is necessary in each reaction. [Don't forget to draw in the lone pairs on this and the next two assessments.]
(d)

Verified step by step guidance

Step 1: Identify the nucleophile and electrophile in the reaction. The nucleophile is the species with lone pairs or a negative charge that can donate electrons, while the electrophile is the species that can accept electrons due to a positive charge or electron deficiency.

Step 2: Locate the lone pairs on the nucleophile. These lone pairs will be the source of electrons for the arrow-pushing mechanism. Ensure all lone pairs are drawn explicitly on the structure.

Step 3: Draw the curved arrow starting from the lone pair of the nucleophile and pointing toward the electrophilic atom or bond. This represents the movement of electrons from the nucleophile to the electrophile.

Step 4: If a bond is formed or broken during the reaction, adjust the structure accordingly. For example, if a bond is formed between the nucleophile and electrophile, show the new bond in the product structure.

Step 5: Verify the formal charges and electron count on all atoms in the product to ensure the mechanism is consistent with the rules of organic chemistry. Adjust lone pairs and charges as necessary.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Arrow-Pushing Mechanism

Arrow-pushing mechanisms are a way to illustrate the movement of electrons during chemical reactions. In these diagrams, arrows represent the flow of electron pairs, indicating how bonds are formed or broken. Understanding this mechanism is crucial for visualizing reaction pathways and predicting the products of organic reactions.

Lone Pairs

Lone pairs are pairs of valence electrons that are not involved in bonding and are localized on an atom. They play a significant role in determining the reactivity and geometry of molecules. In arrow-pushing mechanisms, it is important to represent lone pairs accurately, as they can participate in reactions or influence the stability of intermediates.

Reactants and Products

In organic chemistry, reactants are the starting materials that undergo a chemical change, while products are the substances formed as a result of the reaction. Understanding the relationship between reactants and products is essential for predicting the outcome of a reaction and for drawing accurate mechanisms that depict how reactants transform into products.

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Related Practice

Textbook Question

Suggest an arrow-pushing mechanism for each of the following acid–base reactions

(c)

Textbook Question

Would you expect the following species to be electrophiles or nucleophiles? Some may be both. Explain your answer.

(h)

Textbook Question

Would you expect the following species to be electrophiles or nucleophiles? Some may be both. Explain your answer.

(c)

Textbook Question

Identify the nucleophile and the electrophile in each of the following reactions.

(b)

Textbook Question

Show an arrow-pushing mechanism that forms the product on the right from the reactant at left. Two arrows are necessary in each reaction.

(a)

Textbook Question

Show an arrow-pushing mechanism that forms the product on the right from the reactant at left. Here, three arrows are necessary in each reaction.

(a)

Textbook Question

Identify the arrow types that are shown in each of these arrow-pushing mechanisms.

(iii)

Textbook Question

Acid–base reactions are reversible. Show a mechanism for the reverse of the reactions in Assessment 4.18.

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Show an arrow-pushing mechanism that forms the product on the right from the reactant at left. Only one arrow is necessary in each reaction. [Don't forget to draw in the lone pairs on this and the next two assessments.](d)

Key Concepts

Arrow-Pushing Mechanism

Lone Pairs

Reactants and Products

Watch next

Show an arrow-pushing mechanism that forms the product on the right from the reactant at left. Only one arrow is necessary in each reaction. [Don't forget to draw in the lone pairs on this and the next two assessments.]
(d)